| TT Cup (2023) | 2023/01/24 10:15 | Yuto Kobayashi v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/01/24 08:45 | Oliver Ollman v Yuto Kobayashi | L | 1-3 |
| TT Cup (2023) | 2023/01/17 06:45 | Yuto Kobayashi v Oliver Ollman | W | 2-3 |
| TT Cup (2023) | 2023/01/09 09:15 | Oliver Ollman v Yuto Kobayashi | W | 3-2 |
| TT Cup (2023) | 2023/03/29 09:15 | Stanislav Kruti v Oliver Ollman | L | 3-0 |
| TT Cup (2023) | 2023/03/29 07:45 | Vincent Oberle v Oliver Ollman | L | 3-2 |
| TT Cup (2023) | 2023/03/29 07:15 | Martin Pakk v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/03/29 06:15 | Oliver Ollman v Stanislav Kruti | L | 2-3 |
| TT Cup (2023) | 2023/03/23 10:15 | Oliver Ollman v Vincent Oberle | L | 0-3 |
| TT Cup (2023) | 2023/03/23 09:15 | Raul Pirson v Oliver Ollman | W | 0-3 |
| TT Cup (2023) | 2023/03/23 08:15 | Oliver Ollman v Mart Ojamaa | W | 3-1 |
| TT Cup (2023) | 2023/03/23 06:45 | Vincent Oberle v Oliver Ollman | W | 1-3 |
| TT Cup (2023) | 2023/05/08 08:45 | Yuto Kobayashi v Mart Ojamaa | W | 3-2 |
| TT Cup (2023) | 2023/05/08 08:15 | Mart Ojamaa v Yuto Kobayashi | W | 1-3 |
| TT Cup (2023) | 2023/05/08 07:15 | Yuto Kobayashi v Valdek Putkemaa | L | 0-3 |
| TT Cup (2023) | 2023/05/08 05:45 | Vincent Oberle v Yuto Kobayashi | L | 3-2 |
| TT Cup (2023) | 2023/04/01 13:15 | Yuto Kobayashi v Dmitry Fomichenko | W | 3-1 |
| TT Cup (2023) | 2023/04/01 12:15 | Yuto Kobayashi v Meelis Apsolon | L | 2-3 |
| TT Cup (2023) | 2023/04/01 11:15 | Yuto Kobayashi v Dmitry Fomichenko | W | 3-1 |
| TT Cup (2023) | 2023/04/01 10:15 | Yuto Kobayashi v Anton Kukeste | L | 1-3 |